Diphenylzinc

Diphenylzinc
Skeletal formula of diphenylzinc monomer
Ball-and-stick model of the diphenylzinc monomer molecule
Identifiers
3D model (JSmol)
3603125
ChEBI
ChemSpider
ECHA InfoCard 100.012.803 Edit this at Wikidata
EC Number
  • 214-082-2
28161
  • InChI=1S/2C6H5.Zn/c2*1-2-4-6-5-3-1;/h2*1-5H; ☒N
    Key: MKRVHLWAVKJBFN-UHFFFAOYSA-N ☒N
  • C1([Zn]C2=CC=CC=C2)=CC=CC=C1
Properties
C12H10Zn
Molar mass 219.59 g·mol−1
Hazards
GHS labelling:
GHS02: Flammable
Danger
H228, H250
P210, P222, P240, P241, P280, P302+P334, P370+P378, P422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Diphenylzinc is an organozinc compound. It is commonly used as the synthetic equivalent of a Ph− synthon. Solvent-free diphenylzinc exists as dimeric PhZn(μ-Ph)2ZnPh molecules in the solid state.[1]

Skeletal formula of diphenylzinc dimer
Ball-and-stick model of the diphenylzinc dimer molecule
The dimeric solid state form of diphenylzinc.

Diphenylzinc is commercially available. It may be prepared by reaction of phenyllithium with zinc bromide:[2]

2 PhLi + ZnBr2 → Ph2Zn + 2 LiBr

It may also be prepared by the reaction of phenylmagnesium bromide with zinc chloride or diphenylmercury with zinc metal.[3][4]

References

  1. ^ Markies, Peter R.; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, Friedrich; Smeets, Wilberth J. J.; Spek, Anthony L. (1990). "Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc". Organometallics. 9 (8): 2243. doi:10.1021/om00158a022.
  2. ^ Curtin, David Y.; Tveten, John L. (1961). "Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds". J. Org. Chem. 26 (6): 1764. doi:10.1021/jo01065a017.
  3. ^ Markies, P; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, F.; Spek, Anthony L. (1992). "Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph2Zn·glyme and Ph2Zn·diglyme". J. Organomet. Chem. 430: 1–13. doi:10.1016/0022-328X(92)80090-K.
  4. ^ Pelletier, Guillaume (2013), "Diphenylzinc", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn01548, ISBN 978-0-471-93623-7

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